Andy Cohen ‘regrets’ asking Oprah Winfrey if she’s ever slept with a woman

 (Getty )
(Getty )

Andy Cohen revealed that one of his biggest ever regrets is asking Oprah Winfrey if she had ever slept with a woman.

In a new interview with Entertainment Tonight, the 56-year-old Bravo host reflected on his career and admitted that one of his biggest regrets was asking the billionaire media mogul if she had “taken a dip in the lady pond.”

The awkward moment occurred during a 2013 episode of his Watch What Happens Live talk show in what Cohen described as until that point being a successful episode.

But when Cohen asked her to reveal if she’d ever had a sexual encounter with a woman, things took a turn. He recalled the classic Watch What Happens Live query was “one of my few regrets”.

In a video clip shared by ET, the Color Purple Star stared at Cohen and replied, “No, I have not. Thank you.”

Oprah Winfrey speaks onstage during the 55th Annual NAACP Awards in March 2024 (Getty)
Oprah Winfrey speaks onstage during the 55th Annual NAACP Awards in March 2024 (Getty)

“It meant so much to me that Oprah Winfrey did the show,” Cohen recalled to ET. “It’s gone brilliantly and I turn around and ask her if she’s ever had sex with a woman. I mean, couldn’t I leave it alone?”

After he asked the question and the cameras had stopped rolling, Cohen said that Winfrey did not make him feel awkward for asking about her sexual history.

Later, Gayle King revealed that Winfrey didn’t know what Cohen meant at the time.

“Gayle King told me later that week that Oprah didn’t know what I meant by ‘the lady pond,’ “ he said. “I thought I explained it pretty well there, but listen, I was so grateful that Oprah did the show and I still am.

Despite the awkward moment, Cohen looks back on the interview fondly. “That remains, I think, my favorite episode of WWHL,” he said.

In the same interview, he reflected on how his late-night show hadn’t received proper recognition, unlike other late-night television shows.

“I was very conscious that I wanted to be part of the late-night conversation,” he said to Deadline. He recalled a September 2015 Vanity Fair article spotlighting 10 other male late-night television hosts, including Stephen Colbert, James Corden, Jimmy Fallon, Jimmy Kimmel, Conan O’Brien, John Oliver, Bill Maher, Trevor Noah, Seth Meyers and Larry Wilmore.

After being excluded from the feature, Cohen admitted he felt “salty” since WWHL had been on the air for six years when it was published. He said, “I know what we’re doing; I know what it means to people and I know what it means to me.”